It is an object of the present invention to provide a novel medicament for preventing and/or treating ophthalmologic diseases caused by ocular angiogenesis. According to the present invention, provided is a medicament for preventing and/or treating ophthalmologic diseases caused by ocular angiogenesis, which comprises, as an active ingredient, a pyrazolone derivative such as 3-methyl-1-phenyl-2-pyrazolin-5-one, or a physiologically acceptable salt thereof, or a hydrate thereof or a solvate thereof.

A compound with antitumor activities represented by formula I: ##STR00001##
In formula I, R.sub.1 is alkyl, alkoxy, or ethenyl; and R.sub.2 is alkyl, alkoxy, or halogen.

A compound with antitumor activities represented by formula I: ##STR00001##
In formula I, R.sub.1 is alkyl, alkoxy, or ethenyl; and R.sub.2 is alkyl, alkoxy, or halogen.

A method of analyzing phenylhydrazine content in a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient includes obtaining a first measured value by measuring a phenylhydrazine content of a standard solution including phenylhydrazine or a salt thereof, a first acidic water and a first water-soluble organic solvent and having a phenylhydrazine concentration of 0.01 μg/mL to 10 μg/mL, obtaining a second measured value by measuring a phenylhydrazine content in a sample solution including a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient, a second acidic water and a second water-soluble organic solvent, and detecting a phenylhydrazine content in a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient based on the first measured value and second measured value. The first acidic water is hydrochloric acid, and/or an aqueous acetic acid solution, the first water-soluble organic solvent is acetonitrile and/or methanol, the second acidic water is hydrochloric acid, and/or an aqueous acetic acid solution, and the second water-soluble organic solvent is acetonitrile and/or methanol.

A method of analyzing phenylhydrazine content in a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient includes obtaining a first measured value by measuring a phenylhydrazine content of a standard solution including phenylhydrazine or a salt thereof, a first acidic water and a first water-soluble organic solvent and having a phenylhydrazine concentration of 0.01 μg/mL to 10 μg/mL, obtaining a second measured value by measuring a phenylhydrazine content in a sample solution including a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient, a second acidic water and a second water-soluble organic solvent, and detecting a phenylhydrazine content in a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient based on the first measured value and second measured value. The first acidic water includes hydrochloric acid, the first water-soluble organic solvent is acetonitrile and/or methanol, the second acidic water includes hydrochloric acid, and the second water-soluble organic solvent is acetonitrile and/or methanol.

A method of analyzing phenylhydrazine content in a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient includes obtaining a first measured value by measuring a phenylhydrazine content of a standard solution including phenylhydrazine or a salt thereof, a first acidic water and a first water-soluble organic solvent and having a phenylhydrazine concentration of 0.01 μg/mL to 10 μg/mL, obtaining a second measured value by measuring a phenylhydrazine content in a sample solution including a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient, a second acidic water and a second water-soluble organic solvent, and detecting a phenylhydrazine content in a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient based on the first measured value and second measured value. The first acidic water includes hydrochloric acid, the first water-soluble organic solvent is acetonitrile and/or methanol, the second acidic water includes hydrochloric acid, and the second water-soluble organic solvent is acetonitrile and/or methanol.

A method of analyzing phenylhydrazine content in a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient includes obtaining a first measured value by measuring a phenylhydrazine content of a standard solution including phenylhydrazine or a salt thereof, a first acidic water and a first water-soluble organic solvent and having a phenylhydrazine concentration of 0.01 μg/mL to 10 μg/mL, obtaining a second measured value by measuring a phenylhydrazine content in a sample solution including a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient, a second acidic water and a second water-soluble organic solvent, and detecting a phenylhydrazine content in a 3-methyl-1-phenyl-2-pyrazolin-5-one active pharmaceutical ingredient based on the first measured value and second measured value. The first acidic water is hydrochloric acid, and/or an aqueous acetic acid solution, the first water-soluble organic solvent is acetonitrile and/or methanol, the second acidic water is hydrochloric acid, and/or an aqueous acetic acid solution, and the second water-soluble organic solvent is acetonitrile and/or methanol.

The invention relates to a phenylmethylpyrazolone compound and a method for producing same, said compound having a novel crystal form that corresponds to parameters determined by the method of powder X-ray diffraction analysis, wherein the parameters of the crystal cells correspond to: a (Å)—10.244 (6) Å, b (Å)—11.198 (5) Å, c (Å)—15.911 (9) Å, β°—94.95 (3)°, VÅ 3—1821 (3) Å 3. The angles 2Θ for crystal diffraction patterns correspond to: 4.73°; 5.98°; 9.11°; 9.94°; 11.45°; 14.74°; 15.85°; 17.09°; 21.60°. The interplanar spacings of the crystals correspond to: 8.09 Å; 6.42 Å; 4.58 Å; 3.97 Å; 3.12 Å; 2.79 Å; 2.58 Å; 2.37; 1.99 Å.

The present invention relates to the design and synthesis of a class of novel chiral phosphine ligand, 1,2-bis(diphenylphosphinoalkylamido)-1,2-disubstituted ethane, and use in asymmetric catalytic reactions, such as asymmetric catalytic synthesis of pyrazoline-5-one with a chiral quaternary carbon center, i.e., highly enantioselective synthesis of 3-methyl-4-benzyl-4-(2-butyl-2,3-butadienyl)pyrazoline-5-one by using 3-methyl-4-benzylpyrazoline-5-one and benzyl (2-butyl-2,3-butadienyl) carbonate with tris(dibenzylideneacetone)dipalladium-chloroform adduct and this novel ligand as catalysts. The ligand designed by this present invention has the following advantages: the structure is novel, the synthesis and enlarge are simple, the enantioselective control effect in the practical reaction is excellent, which has a broad application prospect in chiral catalysis.

The present invention relates to the design and synthesis of a class of novel chiral phosphine ligand, 1,2-bis(diphenylphosphinoalkylamido)-1,2-disubstituted ethane, and use in asymmetric catalytic reactions, such as asymmetric catalytic synthesis of pyrazoline-5-one with a chiral quaternary carbon center, i.e., highly enantioselective synthesis of 3-methyl-4-benzyl-4-(2-butyl-2,3-butadienyl)pyrazoline-5-one by using 3-methyl-4-benzylpyrazoline-5-one and benzyl (2-butyl-2,3-butadienyl) carbonate with tris(dibenzylideneacetone)dipalladium-chloroform adduct and this novel ligand as catalysts. The ligand designed by this present invention has the following advantages: the structure is novel, the synthesis and enlarge are simple, the enantioselective control effect in the practical reaction is excellent, which has a broad application prospect in chiral catalysis.